Dimethyl Sulfide → 1-Benzoyl-2,3-diphenylcyclopropane

HRID 1941474Notes

Reaction equation

HRID 1941474 reaction equation
[C:1]1([CH:7]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CSC.[C:13]1([CH:19]=[CH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:21]([CH:20]1[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:19]1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 7189CinnamoylbenzeneHCID 136601Benzene, (diazomethyl)-

Product 1

HCID 109574931-Benzoyl-2,3-diphenylcyclopropane

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent

Procedure

Phenyl diazomethane (prepared as in Example 36, 0.5 mmol in 3 ml of t-butyl methyl ether) was added to a stirred solution of dimethylsulphide (7.3 ml; 0.1 mmol), rhodium (II) acetate (2 mg; 0.005 mmol) and chalcone (103 mg; 0.5 mmol) in dichloromethane (2 ml) at room temperature over a period of 24 hours. After the addition was complete the solvent was removed in vacuo and the residue was chromatographed over silica [eluent dichloromethane:petrol (2:3)], to give the title compound as a 4:1 mixture of trans:cis cyclopropanes as a yellowy solid (58 mg; 39%).

Workup

  1. additionAfter the addition
  2. customwas removed in vacuo
  3. customthe residue was chromatographed over silica [eluent dichloromethane:petrol (2:3)]

Sources & evidence

ORD record
ord-bd4c21647b6e4a18a7115df42d861dc8
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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